logo
By Huuk Team

Road trip from Chicago to Charleston

All Category
iconBoat Tours & Water Sports
iconOutdoor Activities
iconShopping
iconSights & Landmarks
iconNightlife
iconNature & Parks
iconMuseums
Show more (2+)

ITINERARY

17h 5m886 miles17 stops
1
Michigan Avenue Bridge
333 Michigan Ave, Chicago, IL 60601-3901
The view from the bridge is one of the best vistas the city has to offer.
2
Boystown
Chicago, IL
Located in Chicago's North Side, this vibrant neighborhood is known for its exciting nightlife and for being one of the largest LGBTQIA+ communities in the city. It's the host of the annual Chicago Pride Parade, and a must-see in the area is the Legacy Walk on Halsted Street, where you can learn about the contributions of the LGBTQIA+ community while admiring the colorful street art and rainbow crosswalks. Check out the unique shops and then grab a bite at one of the area's delicious Thai or Mexican restaurants. At night, visit one of the neighborhood's bars to enjoy a drag show, concert, and tasty cocktail. Consider taking a food or walking tour of Chicago that stops by Boystown. – Tripadvisor
3
Wrigley Field
1060 W. Addison St., Chicago, IL 60613-4566
Get a behind-the-scenes look at the legendary home of the Chicago Cubs with Wrigley Field Tours. Built in 1914, this must-see Chicago attraction houses more than 100 years of history. New this year, fans can join us on a non-gameday Ivy Tour which includes the opportunity to take a photo in front of Wrigley Field’s historic ivy wall.
4
Angel's Envy Distillery
500 E Main Street, Louisville, KY 40202-1002
Built in the heart of Louisville, the ANGEL’S ENVY Distillery is downtown’s first fully operational whiskey production facility. Co-founded in 2010 by the late Master Distiller Lincoln Henderson, ANGEL’S ENVY began as a passion project that combined their family’s deep-rooted passion for and knowledge of the industry with an innovative outlook on bourbon making and finishing. ANGEL’S ENVY opened the doors in 2016 and puts you in the center of our distilling process for a unique tour experience.
5
Lexington Brewing & Distilling Co.
401 Cross St, Lexington, KY 40508-2806
The first era of the Lexington Brewing Co. began in the 1890s and came to a halt during Prohibition, changing ownership several times in the decades that followed. By the time Pearse Lyons and his son, Mark, explored the brewery in 1999, it was a dilapidated shell of what it had once been. However, Pearse was a visionary and entrepreneur and saw only what it could be. Spurred by a passion for brewing and distilling that courses through the Lyons family lineage of Irish coopers, Pearse revived Lexington Brewing Co. and restored a craft beer tradition that dates back to the 1700s. Pearse continued to dream big as he set his sights on distilling — a natural progression given his background in fermentation, his family’s heritage and Kentucky’s bourbon tradition. Two copper pot stills that were commissioned from Scotland arrived at Lexington Brewing Co. in 2008. In 2012, Town Branch Distillery opened, first new distillery to be built in Lexington, Kentucky, in more than 100 yrs.
6
Fayette Mall
3401 Nicholasville Rd, Lexington, KY 40503-3611
Fayette Mall is located at the intersection of Nicholasville Road and Reynolds Road. The mall is central Kentucky’s premier shopping destination with over 170 retailer and dining options including The Disney Store, H&M, Michael Kors, Sephora and The Cheesecake Factory. Fayette Mall also features a children’s play area located in Center Court. Mobile device charging stations can be found in the Food Court. WiFi is available at Starbucks, Dillard’s and Dick’s Sporting Goods. Customer Service Center is located inside the front entrance next to P.F. Chang’s. Visit shopfayette-mall.com for more information including a complete list of retailers, restaurants, entertainment options and a mall map.
7
Waveland State Historic Site
225 Waveland Museum Ln, Lexington, KY 40514-1618
Experience 19th century plantation life at this historic compound where you can tour the mansion or "big house," see quarters where slaves lived, visit a smokehouse and other elements of daily life in the Old South.
8
House Mountain State Natural Area
9601 Hogskin Road, Knoxville, TN
9
Savage Garden
3237 Garden Dr, Knoxville, TN 37918-3319
10
Cottage Door Antiques & Gifts
4901 Tazewell Pike, Knoxville, TN 37918-9287
11
Muse Knoxville
516 N Beaman St, Knoxville, TN 37914-4410
Muse Knoxville is a children’s Science, Technology, Engineering, Arts, & Math (STEAM) museum located in Chilhowee Park. Our programs in the museum, in schools across East Tennessee, & throughout Knoxville bring STEM, the arts, health & wellness, & emergent literacy to life in the minds of children. We inspire & empower ALL children through transformative learning experiences through a variety of hands-on and inquiry-based, exhibits and Outreach programs for children aged 6 mos. to 10 y/o. *Museum Play - Indoor educational learning & play spaces, a full-dome planetarium, outdoor learning spaces & a playground! *Field Trips - Bring your class, homeschool, daycare or youth group for a day of fun! *Parties/Events - Choose from a variety of packages to celebrate your special day with us. *Planetarium - We house East Tennessee's only public-access planetarium with shows that rotate every hour!
12
Knoxville Botanical Garden
2743 Wimpole Ave, Knoxville, TN 37914-5958
13
Peter Kern Library
407 Union Ave, Knoxville, TN 37902-2112
Hidden inside the historic Kern Building, behind The Oliver Hotel lobby, is Knoxville’s one and only speakeasy, The Peter Kern Library. Once a well-kept secret, the bar is now a beloved institution. The dark wood, fireplace, rows of books, and cocktails named after literary characters create a warm and cozy atmosphere where time seems to stop.
14
CSA II's Rebel Corner
629 Arbor Station Ln #34, Tallahassee, FL 32312
CSA II®'s Rebel Corner is an Online American Heritage Preservation Retailer featuring many areas of American History and Heritage, especially the Wartime Period of 1861-1865, commonly referred to as The War For Southern Independence or The War Between The States!! We offer a wide variety of options and do special orders as well!! Please feel free to visit us at our website for some of the best deals around!!
15
Grove Arcade
1 Page Ave, Asheville, NC 28801-2382
Grove Arcade is a beautifully preserved historical building in the heart of Downtown Asheville that represents the heart and character of the town. It’s rich history and ornate architecture combined with its eclectic mix of shops and restaurants offer patrons a full-day immersion into Asheville lifestyle and culture.
16
Lexington Glassworks
81 S Lexington Ave, Asheville, NC 28801-3309
Lexington Glassworks, located in the heart of downtown Asheville, NC, was born out of the desire to create timeless and innovative hand-blown glass. Each piece is skillfully crafted using century-old techniques with the singular goal of creating top-notch work. The gallery features high-quality custom lighting and handmade glass for any budget. Lexington Glassworks is a makers studio where the public is invited to view the artists at work.
17
Greenville Zoo
150 Cleveland Park Dr, Greenville, SC 29601-3147
Customize this Trip

OVERVIEW

Get ready for an epic adventure from the bustling streets of Chicago to the charming shores of Charleston! Along the way, you'll discover a rich tapestry of landscapes, cities, and historical treasures that will leave you in awe. From the towering skyscrapers that define Chicago's skyline to the serene beaches of the Atlantic coast, each destination offers its own unique flavor and charm.

As you journey through the heartland of America, you'll traverse rolling hills, lush forests, and sparkling rivers that have shaped the nation's identity. Explore vibrant cities brimming with culture, art, and music, where the past meets the present in a captivating blend. Visit iconic landmarks that stand as testaments to human ingenuity and the pursuit of dreams.

Throughout your adventure, immerse yourself in the stories and traditions of the people who have called this land home for centuries. From the bustling markets of Chicago to the elegant mansions of Charleston, uncover the diverse heritage that weaves together the fabric of American history. This journey promises to be an unforgettable exploration of a nation's vibrant spirit and the boundless possibilities that lie within its borders.

1
Start:Michigan Avenue Bridge
Chicago, Illinois·
4.5
(985) review
The view from the bridge is one of the best vistas the city has to offer.
333 Michigan Ave, Chicago, IL 60601-3901
2
Boystown
Chicago, Illinois·
4.5
(98) review
Located in Chicago's North Side, this vibrant neighborhood is known for its exciting nightlife and for being one of the largest LGBTQIA+ communities in the city. It's the host of the annual Chicago Pride Parade, and a must-see in the area is the Legacy Walk on Halsted Street, where you can learn about the contributions of the LGBTQIA+ community while admiring the colorful street art and rainbow crosswalks. Check out the unique shops and then grab a bite at one of the area's delicious Thai or Mexican restaurants. At night, visit one of the neighborhood's bars to enjoy a drag show, concert, and tasty cocktail. Consider taking a food or walking tour of Chicago that stops by Boystown. – Tripadvisor
Chicago, IL
3
Wrigley Field
Chicago, Illinois·
4.5
(9953) review
Get a behind-the-scenes look at the legendary home of the Chicago Cubs with Wrigley Field Tours. Built in 1914, this must-see Chicago attraction houses more than 100 years of history. New this year, fans can join us on a non-gameday Ivy Tour which includes the opportunity to take a photo in front of Wrigley Field’s historic ivy wall.
1060 W. Addison St., Chicago, IL 60613-4566
4
Angel's Envy Distillery
Louisville, Kentucky·
4.5
(967) review
Built in the heart of Louisville, the ANGEL’S ENVY Distillery is downtown’s first fully operational whiskey production facility. Co-founded in 2010 by the late Master Distiller Lincoln Henderson, ANGEL’S ENVY began as a passion project that combined their family’s deep-rooted passion for and knowledge of the industry with an innovative outlook on bourbon making and finishing. ANGEL’S ENVY opened the doors in 2016 and puts you in the center of our distilling process for a unique tour experience.
500 E Main Street, Louisville, KY 40202-1002
5
Lexington Brewing & Distilling Co.
Lexington, Kentucky·
4.5
(984) review
The first era of the Lexington Brewing Co. began in the 1890s and came to a halt during Prohibition, changing ownership several times in the decades that followed. By the time Pearse Lyons and his son, Mark, explored the brewery in 1999, it was a dilapidated shell of what it had once been. However, Pearse was a visionary and entrepreneur and saw only what it could be. Spurred by a passion for brewing and distilling that courses through the Lyons family lineage of Irish coopers, Pearse revived Lexington Brewing Co. and restored a craft beer tradition that dates back to the 1700s. Pearse continued to dream big as he set his sights on distilling — a natural progression given his background in fermentation, his family’s heritage and Kentucky’s bourbon tradition. Two copper pot stills that were commissioned from Scotland arrived at Lexington Brewing Co. in 2008. In 2012, Town Branch Distillery opened, first new distillery to be built in Lexington, Kentucky, in more than 100 yrs.
401 Cross St, Lexington, KY 40508-2806
6
Fayette Mall
Lexington, Kentucky·
4.5
(91) review
Fayette Mall is located at the intersection of Nicholasville Road and Reynolds Road. The mall is central Kentucky’s premier shopping destination with over 170 retailer and dining options including The Disney Store, H&M, Michael Kors, Sephora and The Cheesecake Factory. Fayette Mall also features a children’s play area located in Center Court. Mobile device charging stations can be found in the Food Court. WiFi is available at Starbucks, Dillard’s and Dick’s Sporting Goods. Customer Service Center is located inside the front entrance next to P.F. Chang’s. Visit shopfayette-mall.com for more information including a complete list of retailers, restaurants, entertainment options and a mall map.
3401 Nicholasville Rd, Lexington, KY 40503-3611
7
Waveland State Historic Site
Lexington, Kentucky·
4.5
(97) review
Experience 19th century plantation life at this historic compound where you can tour the mansion or "big house," see quarters where slaves lived, visit a smokehouse and other elements of daily life in the Old South.
225 Waveland Museum Ln, Lexington, KY 40514-1618
8
House Mountain State Natural Area
Knoxville, Tennessee·
4.5
(135) review
9601 Hogskin Road, Knoxville, TN
9
Savage Garden
Knoxville, Tennessee·
4.5
(3) review
3237 Garden Dr, Knoxville, TN 37918-3319
10
Cottage Door Antiques & Gifts
Knoxville, Tennessee·
4.0
(2) review
4901 Tazewell Pike, Knoxville, TN 37918-9287
11
Muse Knoxville
Knoxville, Tennessee·
4.0
(91) review
Muse Knoxville is a children’s Science, Technology, Engineering, Arts, & Math (STEAM) museum located in Chilhowee Park. Our programs in the museum, in schools across East Tennessee, & throughout Knoxville bring STEM, the arts, health & wellness, & emergent literacy to life in the minds of children. We inspire & empower ALL children through transformative learning experiences through a variety of hands-on and inquiry-based, exhibits and Outreach programs for children aged 6 mos. to 10 y/o. *Museum Play - Indoor educational learning & play spaces, a full-dome planetarium, outdoor learning spaces & a playground! *Field Trips - Bring your class, homeschool, daycare or youth group for a day of fun! *Parties/Events - Choose from a variety of packages to celebrate your special day with us. *Planetarium - We house East Tennessee's only public-access planetarium with shows that rotate every hour!
516 N Beaman St, Knoxville, TN 37914-4410
12
Knoxville Botanical Garden
Knoxville, Tennessee·
3.5
(97) review
2743 Wimpole Ave, Knoxville, TN 37914-5958
13
Peter Kern Library
Knoxville, Tennessee·
4.0
(99) review
Hidden inside the historic Kern Building, behind The Oliver Hotel lobby, is Knoxville’s one and only speakeasy, The Peter Kern Library. Once a well-kept secret, the bar is now a beloved institution. The dark wood, fireplace, rows of books, and cocktails named after literary characters create a warm and cozy atmosphere where time seems to stop.
407 Union Ave, Knoxville, TN 37902-2112
14
CSA II's Rebel Corner
Tallahassee, Florida·
5.0
(2) review
CSA II®'s Rebel Corner is an Online American Heritage Preservation Retailer featuring many areas of American History and Heritage, especially the Wartime Period of 1861-1865, commonly referred to as The War For Southern Independence or The War Between The States!! We offer a wide variety of options and do special orders as well!! Please feel free to visit us at our website for some of the best deals around!!
629 Arbor Station Ln #34, Tallahassee, FL 32312
15
Grove Arcade
Asheville, North Carolina·
4.0
(987) review
Grove Arcade is a beautifully preserved historical building in the heart of Downtown Asheville that represents the heart and character of the town. It’s rich history and ornate architecture combined with its eclectic mix of shops and restaurants offer patrons a full-day immersion into Asheville lifestyle and culture.
1 Page Ave, Asheville, NC 28801-2382
16
Lexington Glassworks
Asheville, North Carolina·
4.5
(983) review
Lexington Glassworks, located in the heart of downtown Asheville, NC, was born out of the desire to create timeless and innovative hand-blown glass. Each piece is skillfully crafted using century-old techniques with the singular goal of creating top-notch work. The gallery features high-quality custom lighting and handmade glass for any budget. Lexington Glassworks is a makers studio where the public is invited to view the artists at work.
81 S Lexington Ave, Asheville, NC 28801-3309
17
Greenville Zoo
Greenville, South Carolina·
4.0
(996) review
150 Cleveland Park Dr, Greenville, SC 29601-3147

CHECKLIST

icon
GPS device or app
icon
Download Offline Map
icon
Car charger and portable battery
icon
Water bottles and snacks
icon
Travel pillow and blanket
icon
Sunglasses and sunscreen
icon
First-aid kit
icon
Trash bags
icon
Hand sanitizer and wet wipes
icon
Driver’s license and vehicle registration
icon
Cash and cards
icon
Camera or smartphone
Unlock Effortless Travel Planning
Create your dream trip in minutes by this prompt. Try now!
FAQ
Frequently Asked Questions
What's the driving distance between Chicago and Charleston?
The distance is 886 miles
What's the travel time between Chicago and Charleston?
The driving time can vary depending on traffic conditions, but it is typically 17h 5m mins in normal traffic
What are some of the best cities to visit between Chicago and Charleston?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Charleston?
There are plenty! Here are some stops you shouldn’t miss on your way to Charleston
What’s the weather like in Charleston?
The weather in Charleston is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Charleston in January
Weather in Charleston in February
Weather in Charleston in March
Weather in Charleston in April
Weather in Charleston in May
Weather in Charleston in June
Weather in Charleston in July
Weather in Charleston in August
Weather in Charleston in September
Weather in Charleston in October
Weather in Charleston in November
Weather in Charleston in December
Interested in a detailed plan for your time in Charleston?
Plan your dream Charleston trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Charleston
A 2-day itinerary in Charleston
A 3-day itinerary in Charleston
A 4-day itinerary in Charleston
A 5-day itinerary in Charleston
A 6-day itinerary in Charleston
Where else can I travel to if I'm starting my trip in Chicago?
We have a lot of great trip options for Chicago! See the links below for all the itineraries we created for you
logo
Features
Roadtrip PlanBlogAI Agent for TravelNear byFeedback
About
About HuukPolicyTermsPrivacy
Contact us
DiscordFacebookTiktokInstagramYoutubeLinkedin